The Outdoorswoman’s Winter Guide to Woodstock, VT

Woodstock, Vermont looks like a scene out of an old-timey children’s book. Its pint-sized downtown is lined with B&Bs, local shops, and Federal and Greek-revival houses. An afternoon walk takes you by stately homes on each side of the Ottauquechee river, giving you a view of its (no less than) three covered bridges.

Blanketed in fresh snow, this quiet town feels even quieter. It’s a welcome respite from city life, snug between low mountains and farmland. I felt my blood pressure drop as soon as I pulled off the highway.

Once the second-home of the Rockefellers, Woodstock is the beloved destination of a certain milieu: you’ll see upper-crust visitors pulling up in their Land Rovers with New York license plates.

Beyond the out-of-towners and weekenders, you’ll find a community that’s quintessentially Vermont. And surprisingly (for one of the state’s priciest zip codes), outdoor activities are accessible and unassuming, making this small town a desirable getaway for an adventure.

Outside

Upper Valley and Woodstock residents swear by this small but mighty mountain. Generations of local skiers learned to “pizza” and “french fry” here, which ushered in a fierce regional following.

In the last year, Suicide Six upped their game, hiring fresh leadership and investing in new snow machines and a quad lift. Thankfully, that doesn’t take away from the feeling of true locals mountain. The slope is ideal for beginning-to-intermediate skiers and is priced at a reasonable $68 for a day pass.

The first word that comes to mind when I think of this Nordic skiing and snowshoe center in “peaceful.” Its gentle, meadow trails (30 km of them), adjacent woodlands, and open skies make it an easy place to get into a rhythm on a pair of skis. If you get there bright and early, you’ll be the first one making tracks on its groomed snow. They offer group and private lessons. (My wonderful teacher Dorothy’s patience astounded me). Snowshoers and fat bikers can also adventure on its trails, crossing over rivers and along the sloping side of Mt. Peg. It’s $20 for a day pass.

You can tell which peak is Mt. Tom by the star of Christmas lights at its peak. From anywhere in town, you can see the star glowing during the winter. Although Mt. Tom is low in elevation (1,400 feet), it’s a quick 30 minutes from town in snowshoes, giving you sweeping views of Woodstock and the surrounding farmlands. There are three separate routes, one of which starts at the Marsh-Billings-Rockefeller National Historical Park (see below).

This beautiful park is the result of ongoing forest stewardship, and it was one of the first landscapes in the country to benefit from intentional preservation. The Marsh-Billings-Rockefeller National Historical Park, which also includes a historic mansion, is run in partnership with the National Park Service and The Woodstock Foundation. Here, you can hike or snowshoe surrounded by 400-year-old conifers. Make sure to stop at the high-valley pond before you make your way to the top.

On the way to Woodstock on Route 4, you can glimpse into Quechee Gorge. This 165-foot drop is the biggest waterfall in Vermont and is at the heart of the Ottauquechee State park. For a scenic experience, snowshoe or hike along the river up to Dewey’s Pond.

Billings Farm & Museum is a small museum right outside Woodstock’s village (and across from the National Park). A functioning dairy farm — with some prize-winning Jersey’s to boot — it gives you a sense of Vermont’s agricultural heritage, its changing landscape, and Woodstock’s ties to preservation. My favorite part was getting to pet the biggest cow Bounty for 15 minutes.

Inside

Food & Drink:

Every New England town needs an old-fashioned tavern. Tucked away in a corner of the Woodstock Inn, Richardson’s does the trick. Try to grab a table by the fireplace and warm up with a beer and a big cup of chicken noodle soup. I also loved their cook’s salad and pork schnitzel sandwich.

If I had a last supper, I would want it to be here: eating a bowl of Vermont cheddar soup and a mug of hot cider perched above the Ottauquechee river. Although this fine dining establishment serves a beautiful dinner, my favorite meal is lunch. Get there early or late, and ask for the corner table. While you wait, slip downstairs to see the glassblowers in action. The mill is still functioning, and their glass-blowing demonstrations bring another level of appreciation to that wine glass on your table.

If you want a no-frills burger after snowshoeing, this is your destination. Worthy Kitchen is a counter-service restaurant that offers cozy farm-to-table fare from poutine to fried chicken to their famous doughnuts. During ski season, this place is packed but well-worth the wait.

Stay:

This rustic B&B is perfect for the frugal traveler. It’s historic, comfortable, and within a short drive from town, Suicide Six, and the Nordic Center. If you need anything, ask Peter and Carol for help — they’re known for their warm welcome and helpful suggestions.

This iconic inn overlooks the town green with its graceful facade and stellar reputation. It’s worth the splurge just to sit in front of the massive double fireplace with a good book and a Vermont Flannel Blanket. Recently remodeled, the inn keeps the old-school charm with warm updates that make it feel less stuffy and more inviting. It’s the ideal setting anyone who loves relaxing as much as adventuring. In that case, I recommend sitting in their outdoor hot tub after a long day skiing.